Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives

Synthesis

Volumn , Issue 2, 2006, Pages 344-348

  Baghbanzadeh, Mostafa ^a   Salehi, Peyman ^a   Dabiri, Minoo ^a   Kozehgary, Gholamreza ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Bisdihydroquinazolinones; Catalysis; Heterocycles; Multicomponent reactions; Water

Indexed keywords

CATALYSIS; DERIVATIVES; REACTION KINETICS; SOLVENTS; SYNTHESIS (CHEMICAL); WATER;

BIDIHYDROQUINAZOLINONES; HETEROCYCLES; MULTICOMPONENT REACTIONS;

KETONES;

ACID ANHYDRIDE; ALDEHYDE; AMINE; BIS 2,3 DIHYDROQUINAZOLIN 4(1H) ONE; HETEROCYCLIC COMPOUND; QUINAZOLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CONFORMATIONAL TRANSITION; DERIVATIZATION; DRUG ISOLATION; GROWTH REGULATION; PROTON NUCLEAR MAGNETIC RESONANCE; SCREENING; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 31544435491     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-924766     Document Type: Article

References (36)

1. (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
2. (b) Kolb, H. C.; Sharpless, K. B. Drug Discov. Today 2003, 8, 1128.
3. (a) Hamel, E.; Lin, C. M.; Plowman, J.; Wang, H.; Lee, K.; Paull, K. D. Biochem. Pharmacol. 1996, 51, 53.
4. (b) Biressi, M. G.; Cantarelli, G.; Carissimi, M.; Cattaneo, A.; Ravenna, F. Farmaco, Ed. Sci. 1969, 24, 199.
5. (c) Bhalla, P. R.; Walworth, B. L. American Cyanamid Co. Eur. Pat. Appl. Ep58.822, 1982; Chem. Abstr. 1983, 98, 1669.
6. (d) Bhalla, P. R.; Walworth, B. L. American Cyanamid Co., US Patent 4.431.440, 1984; Chem. Abstr. 1984, 100, 174857.
7. (e) Hour, M.; Huang, L.; Kuo, S.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K. J. Med. Chem. 2000, 43, 4479.
8. (a) Rao, V. B.; Hanumanthu, P.; Ratnam, C. V. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1979, 18, 493.
9. (b) Lopez, S. E.; Rosales, M. E.; Urdaneta, N.; Godoy, M. V.; Charris, J. E. J. Chem. Res., Synop. 2000, 258.
10. (c) Abdel-Jalil, R. J.; Volter, W.; Saeed, M. Tetrahedron Lett. 2004, 45, 3475.
11. (a) Wolf, J. F.; Rathman, T. L.; Sleevi, M. C.; Campbell, J. A.; Greenwood, T. D. J. Med. Chem. 1990, 33, 161.
12. (b) Padia, J. K.; Field, M.; Hinton, J.; Meecham, K.; Pablo, J.; Pinnock, R.; Roth, B. D.; Singh, L.; Suman-Chauhan, N.; Trivedi, B. K.; Webdale, L. J. Med. Chem. 1998, 41, 1042.
13. (c) Kung, P.-P.; Casper, M. D.; Cook, K. L.; Wilson-Lingard, L.; Risen, L. M.; Vickers, T. A.; Ranken, R.; Blyn, L. B.; Wyatt, R.; Cook, P. D.; Ecker, D. J. J. Med. Chem. 1999, 42, 4705.
14. (d) Tsou, H.-R.; Mamuya, N.; Johnson, B. D.; Reich, M. F.; Gruber, B. C.; Ye, F.; Nilakantan, R.; Shen, R.; Discafani, C.; Deblanc, R.; Davis, R.; Kohen, F. E.; Greenberger, L. M.; Wang, Y.-F.; Wissner, A. J. Med. Chem. 2001, 44, 2719.
15. (e) Matsuno, K.; Ichimura, M.; Nakajima, T.; Tahara, K.; Fujiwara, S.; Kase, H.; Vishiki, J.; Giese, N. A.; Pandey, A.; Scarborough, R. M.; Lokker, N. A.; Yu, J.-C.; Irie, J.; Tsukuda, E.; Ide, S.-I.; Oda, S.; Nomoto, Y. J. Med. Chem. 2002, 45, 3057.
16. Maskey, R. P.; Shaaban, M.; Grun-Wollny, I.; Laatsch, H. J. Nat. Prod. 2004, 67, 1131.
17. Reddy, G. M.; Bhavani, A. K. D.; Reddy, P. P.; Reddy, P. S. N. Synthesis 2002, 1311; and references sited therein.
18. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Baghbanzadeh, M. Synlett 2005, 1155.
19. (a) Holbrey, J. D.; Seddon, K. R. Clean Prod. Proc. 1999, 1, 223.
20. (b) Elare, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391.
21. (c) Welton, T. Chem. Rev. 1999, 99, 2071.
22. (d) Wasserschied, P.; Kiem, M. Angew. Chem. Int. Ed. 2000, 39, 3772.
23. (e) Sheldon, R. Chem. Commun. 2001, 2399.
24. (f) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182, 419.
25. (g) Wilks, J. S. J. Mol. Catal. A: Chem. 2004, 214, 11.
26. (h) Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Tetrahedron 2005, 61, 1015.
27. (a) Breslow, R. Acc. Chem. Res. 1991, 24, 159.
28. (b) Gajewski, J. J. Acc. Chem. Res. 1997, 30, 219.
29. (c) Otto, S.; Engberts, J. B. F. N. Org. Biomol. Chem. 2003, 1, 2809.
30. (d) Pratt, L. R.; Pohrille, A. Chem. Rev. 2002, 102, 2671.
31. (e) Ludwig, R. Angew. Chem. Int. Ed. 2001, 40, 1808.
32. (a) Pandey, G.; Singh, R. P.; Gary, A.; Singh, V. K. Tetrahedron Lett. 2005, 46, 2137.
33. (b) Werner, B.; Domling, A. Molecules 2003, 8, 53.
34. (c) Domling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3169.
35. (d) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
36. (e) Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.